Concepts in Organic Synthesis

Protecting Groups

1. A protecting group or protective group is introduced into a molecule by

chemical modification of a functional group to obtain chemoselectivity in a
subsequent chemical reaction.

2. It plays an important role in multistep organic synthesis.

3. Acetal protection of a ketone during reduction of an ester, vs. reduction to a

diol when unprotected. In many preparations of delicate organic compounds,
some specific parts of their molecules cannot survive the required reagents or
chemical environments.

4. Then, these parts, or groups, must be protected. For example, lithium

aluminium hydride is a highly reactive but useful reagent capable of reducing
esters to alcohols. It will always react with carbonyl groups, and this cannot be
discouraged by any means.

5. When a reduction of an ester is required in the presence of a carbonyl, the

attack of the hydride on the carbonyl has to be prevented. For example, the
carbonyl is converted into an acetal, which does not react with hydrides.

6. The acetal is then called a protecting group for the carbonyl. After the step
involving the hydride is complete, the acetal is removed (by reacting it with an
aqueous acid), giving back the original carbonyl.

7. This step is called deprotection. Protecting groups are more commonly used in
small-scale laboratory work and initial development than in industrial
production processes because their use adds additional steps and material costs
to the process.